The casting of the genre- and gender-defying artist is a breakthrough moment for transgender actors on Broadway.

Justin Vivian Bond
Eric McNatt

When Mx. Justin Vivian Bond takes the stage as Anna Madrigal in the musical adaptation Armistead Maupin’s Tales of the City March 27 at the Music Box Theatre, v (Bond’s preferred pronoun) will make history as the first actor who identifies as transgender to play a trans character on Broadway.

Madrigal’s famous words to her new tenant Mary Ann Singleton, “Good. You’re one of us then. Welcome to 28 Barbary Lane,” will be an affirmation.

Tales of the City’s New York arrival—even if only for a one-night-only benefit concert—has been anticipated since its 2011 premiere at San Francisco’s American Conservatory Theatre. In the show’s world premiere, Anna Madrigal—who reveals that she is transgender—was played by Tony Award-winning actor Judy Kaye.

“I thought it was fantastic,” Bond says of the ACT premiere. “I thought Judy Kaye was amazing, but even so, I was a little disappointed that they didn’t have a trans woman playing the part of Anna Madrigal. And I was too young at the time, so I wasn’t personally insulted. But, now, she’s kind of, we’re about the same age. I’m a little bit younger than she was in the first book.”

When the opportunity came to stage the musical in New York as a benefit for the Eugene O’Neill Theater Center, Bond was the first to get the call to play Mrs. Madrigal, and v was “thrilled.”

Justin Vivian Bond and Betsy Wolfe
Isaak Berliner

One could argue that the writers had Bond in their collective subconscious all along. The musical's score is by Scissor Sisters front man Jake Shears and John Garden, and the book is by Tony Award-winning Avenue Q writer Jeff Whitty. Bond, Shears, and Whitty have been friends since their early start in the East Village.

“When Scissor Sisters made it, it was very exciting because we all lived on the same block and had coffee every morning with Jason [Jake Shears] and Ana [Matronic], and so it was like, ‘Oh hey girl!’ And Sammy Jo, who was my lover at the time, ended up touring the world as their DJ, so we were all just nuts that had breakfast together every day. And then the next thing you know everybody is world famous or winning Tonys like Jeff did. Then it’s like ‘Woah!’ So it’s kind of nice to all be coming together on that night.

The beloved 1970s-set San Francisco literary series was more than just a love letter to a city and its people. Maupin captured a golden moment in LGBT history, before the dawn of the AIDS crisis, when he says the city felt like a utopia that mixed gay and straight culture, and love and acceptance were the norm. And Mrs. Madrigal was Maupin’s pied piper, beckoning readers to seek out new lives in San Francisco.

Bond was lured to San Francisco by a phone call from a friend who was already living there. (Bond points out that it was this friend’s mother who served as the inspiration for v’s boozy chanteuse creation, Kiki DuRane.) “She called me one day, and she said, ‘Honey you got to move to San Francisco. New York is the father and San Francisco is the mother, and you need some mothering.'

Justin Vivian Bond
Eric McNatt

“And so I moved there, also with the knowledge that as a kid I heard my uncle saying, ‘San Francisco is sin city. It’s where all the gays live and an earthquake was going to come along and take San Francisco in the ocean as God’s retribution,’ and I was like, ‘Ooooh!’ When I got there, of course, it wasn’t the same spirit as the books were when Armistead wrote them in the '70s, but I was young. So, I met a lot of people like those characters and my Anna Madrigal was Kate Bornstein.”

Tales of the City marks Bond’s first return to Broadway since earning a Tony nomination for Kiki & Herb: Alive on Broadway ten years ago.

So, would Bond make the leap back uptown and do a full run of Tales of the City on Broadway? “I doubt it,” v says. “It’s such hard work. I think of it as being such hard work, but it is a wonderful, I love the people. I saw Hello, Dolly! the other day. I’d be happy to step into that role!”

Bond, who wasn’t aware that v’s casting as Madrigal would make Broadway history, says, “I think for a long time the excuse for not casting trans people was because they didn’t have the chops, but now because there are becoming more and more trans roles, people are becoming more open minded about how they cast their shows in the first place. They are rethinking historical plays or reviving plays with nontraditional casting. I think it gives trans people an opportunity to develop this artist and hone their craft. As more trans artists are starting to be able to work more, they become better at what they do.”

EXCLUSIVE: These Tales of the City Musical Portraits Mark an Unprecedented Broadway Milestone

EXCLUSIVE: Portraits from the One-Night-Only Tales of the City

EXCLUSIVE: Portraits from the One-Night-Only Tales of the City

The musical based on Armistead Maupin’s beloved novel series received a history-making, one-night-only Broadway concert presentation—and Playbill was there to witness the milestone.

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